


Not Too Sure, Not Too Proud

by verucasalt123



Category: Supernatural
Genre: Awkward Sexual Situations, First Time, Humor, M/M, Sibling Incest, Wincest - Freeform
Language: English
Status: Completed
Published: 2013-03-05
Updated: 2013-03-05
Packaged: 2017-12-04 09:11:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,692
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/709048
Author URL: https://archiveofourown.org/users/verucasalt123/pseuds/verucasalt123
Summary: <blockquote class="userstuff">
              <p>Neither of them were in any danger of losing their soul tonight, if Buffy reruns were anything to go by. (Title stolen from a very old Better Than Ezra song)</p>
            </blockquote>





	Not Too Sure, Not Too Proud

**Author's Note:**

> Original Prompt: _Sam/Dean, first time. But, instead of being this hot, perfectly magical moment, it turns into a big disaster when they can't figure out the logistics, or who's going to top or anything. Bonus points if either or both do internet research trying to figure out the ins and outs *coughs* of gay sex._
> 
> Art by the lovely and talented lightthesparks.

[](http://pics.livejournal.com/verucasalt123/pic/0002s7zt/)

Dean had gone to retrieve his brother from Stanford just for a couple of days. He needed help. And yeah, maybe he could have done it without Sam, but as he’d said at the time, he didn’t want to. Neither of them had ever dreamed that the anomalous weekend visit would result in events that would devastate Sam down to the depths of his soul. He was heartbroken, but determined. From the years of watching his father hunt in a quest for revenge, Dean knew this was not a healthy reaction, Sam throwing himself into the hunt with vigor after having lost Jessica. Dean didn’t know Jessica, had met her only for that brief moment in the apartment she and Sam had shared, but he _did_ know how much his brother had loved her, though he channeled all his grief into ‘the job’ instead of properly mourning.

Had their places been reversed, it’s exactly what Dean would have done, even though he knew how terribly that had worked out for their father, stealing away both their childhoods and ending up with nothing but his obsession. Though he understood why his brother felt the way he did and was reacting much as their father had after their mother had been killed, he was not about to let Sam go down the same road, not if he could do anything to stop it. He wasn’t going to let Sam turn his adulthood into a continuation of his heartbreaking childhood.

Months later, it seemed there was one childhood memory neither of them could shake off. They’d both skated around the edges of it for a good long while – that not-quite-brotherly feeling that had left the two of them confused and afraid as teenagers. It had never been acted upon then, and Sam leaving for Stanford had taken away the option. Of course now, Dean didn’t feel it would be appropriate to bring it up since Sam wouldn’t talk about Jess and he had no way to know how far along he was in the healing process. 

There had just never been any kind of perfect moment for him to ask Sam “Hey, remember before you left for Stanford there was all this unresolved sexual tension between us?” or to follow it up with “We could **resolve** that now, you know”. 

It took them both my surprise when, after narrowly escaping a murderous water spirit, the adrenaline or the relief or the protective instinct drove them into each other’s arms. All they knew what that all of a sudden, they were kissing passionately, Sam’s hands on both sides of Dean’s face, Dean’s fingers in Sam’s stupid long hair. It only took a few moments of rutting up against each other before they both came in their pants like a couple of ridiculous teenagers.

Luckily, the adrenaline soon faded and they just fell onto their separate beds and into a deep sleep.

 

[](http://pics.livejournal.com/verucasalt123/pic/0002w043/)

The next day was not so lucky, because though Dean knew it was coming, he wasn’t prepared to have this conversation with Sam. Not even when Sam, the Undisputed World Heavyweight Champion of Heartfelt Speeches, fired his opening salvo with “So, uh, we really, you know, um, did… _that_ , I guess.”

Dean retreated to his fallback position of apologizing and taking on blame for anything that might not be okay. “Yeah, we did. I’m really sorry, honestly, it was out of line and I shouldn’t have-”

His words were cut off and hurriedly retreating into his brain when Sam’s entire demeanor changed in an instant and he was fixed with a level glare.

“Don’t you dare. Don’t you _fucking_ dare give that to me and then take it back.”

“So you…you do want that? This? With me?” Yeah, okay, monosyllabic and vague was all Dean had after hearing Sam’s response, seeing the simultaneous lust and anger in his expression. And since when did he know what ‘lustful’ looked like on his brother? Well, since the night before, obviously.

“I was there too, you know, I think you might have noticed that I _wanted_ it.”

And so it began, long months of hunting and driving, occasionally interrupted by rough kisses, fondling, hand jobs, and one memorable occasion when Sam placed his strong forearm against Dean’s hips and sucked his cock with enthusiasm, if not with skill or technique. 

They talked about it a little. Had Dean had gone to bed with a guy before? No. (Neither had Sam) Had Sam fooled around with guys before? Yes. (So had Dean) What about that other kind of sex?

“What other kind?”

Dean flushed and continued his line of questioning. “The butt sex kind, Sammy. You’ve never-”

“Been the catcher?” Sam replied, with a teasing smirk. “No. Jess and I tried it, once, like that, but she didn’t like it so we stopped and we never did it again.”

Sam mentioning Jessica in a nice, nostalgic but not heartbroken way gave Dean a little hope. Of course, he wouldn’t acknowledge it, and decided to take the conversation back into his more familiar territory. “Not surprising, I guess, considering what you’re packing.”

 

[](http://pics.livejournal.com/verucasalt123/pic/0002xz2z/)

That earned him one of his favorite bitchfaces and an accompanying _free-if-you-order-right-now_ eyeroll. The expression didn’t stop Sam’s cheeks from heating up, though. “Damn it, Dean, we’ve talked about this. It’s just proportional, all right?”

Dean held up his hands in a mock-surrender. “Sorry. I was just thinking that we can’t just…” he searched for the right words, “we can’t just stay like this, in a holding pattern. Things are going to progress, that’s how this works, and even though we’re not exactly the poster children for healthy sexual relationships, I can’t imagine that both of us wouldn’t want to go further at some point.” He didn’t mean to imply that his ‘some point’ had already occurred, because he had no idea that Sam was past that metaphoric highway mile marker as well.

“So you’d be okay with it?” Sam asked. “If we, uh…you know, if we actually had sex. That would be all right with you? I’m not going to pressure you into it, and if you think I won’t know that you’re only doing it because it’s what you imagine I want, think again.“

“Yeah, I’d be okay with it. More than okay.”

“Me too.”

An awkward silence ensued for the rest of their motel room breakfast – coffee for Sam, last night’s leftover pie takeout from the diner for Dean. They packed up and moved on to the next hunt without discussing it further.

Three weeks later, somewhere close enough to the Alamo that there were billboards announcing the attraction, they were rolling around naked in bed with Sam’s cock pressed into Dean’s leg and Dean’s mouth leaving bite marks on Sam’s collarbone (no sense in showing up with all their fake FBI credentials and suits if one of them was going to have a giant hickey. It was fairly likely that would kind of undermine their whole ‘we are the authorities’ gig while interviewing witnesses). After they were both spent, Sam rolled to the side and cupped Dean’s jaw, whispering “I want to have sex. Can we have sex? I mean, not now, but, you know, sometime?”

“Yes” was the only answer Dean had for that question.

The issue here was that neither one of them had much experience, and they weren’t sure exactly how to go about creating this monumental step in their crazy, dysfunctional gay incest relationship. So, nothing changed over the next week or two.

Not surprisingly, one night over Chinese takout in a motel room near Columbus, Georgia, Sam brought up the subject again. “I did some, uh, research”, he said, flushing a bit and not looking at Dean. 

“Yeah, you always do the research, Sammy.”

“Not for the hunt. For the other thing…you know, what we talked about before. The sex thing. I read some websites that were for, uh…beginners? Like us, people who want to but aren’t really sure...well, the logistics or whatever, the practical aspects.”

“So now you’re concerned with practical aspects? How can it be all that much different, really? Tab A, Slot B, so maybe it’s not the same, uh – slot – but the mechanics, I mean, it can’t be that complicated.”

“I’ll let you read some of the links I saved. You can tell me what you think after that, okay?”

Dean agreed, because he knew Sam was unaware of the research he’d done on his own. Not articles, but gay porn clips on the web. He read the articles, though, and they sure made it sound like it was slightly more complicated than what he’d seen in downloaded videos. The downloaded videos he wasn’t going to tell Sam about for fear of another accusation of confusing reality with porn.

To his surprise, Dean found that there was really a lot more involved than he initially anticipated. After a week, he told his brother he really did want to try it, he’d read all the stuff and wanted to show off his newfound knowledge. 

They’d gone out for dinner and more than a few beers, then headed back to their motel room. The usual kissing, groping, shed clothing and mutual satisfaction ensued, but Dean was not going to back down from this. He’d even gone and bought a bottle of Astroglide after being treated to an explicit demonstration of _preparing_ your sexual partner, both via internet articles and porn movies. 

Reaching across to the nightstand next to the bed they were currently using, Dean grabbed the bottle of lube and coated his fingers with it. Moving so that he had better access, he slipped one finger, just up to the first knuckle, into Sam’s hole.

“Ahhhhhh! Jesus, Dean, that’s…just, you know, give a guy a warning, all right?” Sam practically shouted, with his eyes wide and his hands trembling. 

“This is what you’re supposed to do, though, right? Preparing? I mean, I know I told you when we were teenagers that you need to go down on a chick for a few minutes to get her ready, but you’re not a chick, and I’m not going down on you before I fuck you.”

“Oh, so _you’re_ fucking _me_? Don’t you think we should have discussed this ahead of time?”

Dean was exasperated. He pulled his finger out and sat up next to Sam on the bed. “What did you think? That you were going to fuck **me**? We’ve had this conversation. I’m not nearly ready for your Godzilla cock up my ass. So yeah, I think if we’re going to do this, at least this one time, I’m going to be the one doing the fucking. I’m not saying I won’t ever, you know, but I think I need a little more time getting comfortable with this before I let you fuck me.”

“Right, because it’s so much easier for me to understand? Honestly?” 

 

[](http://pics.livejournal.com/verucasalt123/pic/0002y3cz/)

“I’m older anyway! I’m the older brother! If brothers are gonna fuck, the older one should fuck the younger one. That’s just plain butt-sex, incest common sense, Sam”, Dean replied, knowing his argument was a giant pile of bullshit.

And goddamnit . Both of them thought this would be some perfect moment of happiness, this meaningful act that would take them in a new direction. But neither of them expected to experience such a high level of “what the fuck”. 

“Dean, you know I want this as much as you do. But maybe we should discuss it a little more? Come up with a game plan or something?”

“ _Game plan_? Seriously? Sam, it’s sex. If you try to make us a checklist with specific details, it takes all the fun out of it.”

“Yeah, I – I know, I just…it’s a weird feeling, okay?”

‘And you think me sticking my fingers in your ass isn’t weird to me? First times are complicated, but we don’t need a fucking Venn Diagram for it.”

“You know what a Venn Diagram is?” asked Sam, switching over from his sex brain to his geek brain in half a second.

“I did go to school until eleventh grade, bitch, I’m not an idiot.”

“Awww, fuck, Dean, that was a really shitty thing for me to say. I’m sorry. I’m just not used to hearing you talk about stuff like that.

“Yeah, well, I’m not used to fucking my brother, so excuse me for not being exactly sure of what I’m doing here, alright?”

Sam gave it a few moments’ thought, and then replied, “Okay. So you want to keep going? Or do you want to wait a while? I’m all right with you being, you know…on top or whatever. I’m the one who said I wanted this to happen, anyway, right?

“I don’t want to stop. We’ve gone this far, and if you’re okay with the situation as it is, why don’t we just give it a try? Hey, you said you tried once with Jess but she didn’t like it so you stopped. It didn’t ruin what you had or anything. So why would that be true for us?”

“No, you’re right. I do want to keep going”, Sam said, taking a deep breath and closing his eyes. He settled back down onto the bed. When nothing happened after a minute, he looked up again at Dean, who seemed to still be a bit apprehensive.

“I don’t want to hurt you”, he said, his voice small and quiet.

“You won’t. If you do, I’ll tell you, I swear. Just…come on, let’s just do this.”

Dean grabbed the lube again and, a bit more slowly this time, pushed gently into Sam, carefully. After a minute or so, he could feel his brother start to relax again, and he went over the instructions in his mind once more. “Breathe out, Sam, okay?”

Sam let a shaky exhale escape him and fisted the sheets as Dean slid in another finger alongside the first one. He knew Dean was being gentle and could feel that he was using a ridiculous amount of lube. Still, it hurt, not terribly, and it was really more just a strange, odd sensation than anything actually painful. 

“You okay?” Dean asked, as he continued to very slowly move his two fingers in and out of Sam’s ass. 

“Yeah, I – it feels weird but I think it’s-” Oh, Christ, what was that? Dean had angled his fingers in such a way that he touched something that made Sam almost jump out of bed. “What was that? What the fuck was that, Dean?”

With a slight chuckle, Dean responded, “I think maybe I got your…you know, that, uh, the G-spot for the gay sex?”

Still shaking, Sam understood. After all, he _had_ done his research. “Prostate. That’s what it’s called. Can you do it again?”

Oh hell yes. Now Dean was feeling a bit more confident. Pouring on a little more lube, he eased another finger inside of Sam, trying to duplicate his previous action.

It wasn’t working. Sam did seem more relaxed, though, and his eyes were blown and dark, sweat breaking out over his brow. Dean kept on moving and finally managed to find that place again, judging by the way Sam moaned and cursed. He even started pushing back a bit, moving into Dean’s touch almost instinctively. 

Now, Dean was serious about not wanting to hurt his brother. He took his time, getting Sam as relaxed and open as he imagined he possibly could before finally asking the real question. “Are you ready? Can I – uh, can I just go ahead and…”

“Yeah, yes, do it, please, before I chicken out. Just, uh, try to-”

 

[](http://pics.livejournal.com/verucasalt123/pic/0002z0rz/)

“Of course, I know, I know Sammy”, he replied, as he was eagerly slicking up his cock to get ready for the main event. “But the stuff all said it’s easier if you’re turned over, at least for the first time. Supposed to be feel better that way, not hurt as much, you know, for…people like us.”

“Beginners?” Sam asked, breath hitching and legs shaking, but still trying to make sure this was going to be good for both of them. “All right.” He turned over and buried his face in the pillows while Dean pulled his hips up for better access. 

“Just remember to breathe and relax, okay?”

“You sound like a yoga instructor, dude”

“Shut your mouth, Sam, I’m a butt sex instructor. That’s way cooler.” Guiding his cock to Sam’s now loose (well, _looser_ ) and lubed hole, he pushed slowly past the ring of muscle just a tiny bit.

At that point, Sam was biting the pillow to keep from screaming, and the only sounds Dean heard were broken off moans. It took him several minutes of incrementally pushing forward before he was finally all the way inside. For a moment, he was completely still. He didn’t like not being able to see Sam’s face. “Still doing all right, baby?”

Sam swallowed hard and nodded, unable to speak. It hurt so fucking bad, but even after just a minute or two, the pain faded into just a slight burning sensation, and his cock started to get hard again when he realized exactly what this was. Dean was fucking him. This was really happening. 

At the same time, Dean was thinking only that no experience he’d ever had with any girl measured up to this feeling. Sam was so fucking tight, and the pressure on his dick was almost unbearable. “Okay if I move now?” he asked, not exactly sure how he would handle it if the answer was no.

“Go ahead, I’m all right.”

Dean started off very slowly, just rocking back and forth with slow, deliberately shallow motions. His body, however, was flipping him the bird and he couldn’t help but speed up a little bit. 

Sam barely felt the pain anymore, though it was still there. It just felt so damn good. However ‘good’ fit in with this incredibly intrusive and foreign feeling that took over once Dean started moving in earnest.

And god damn it. It couldn’t have been more than two minutes, three tops, before the heat and grip around his cock caused Dean’s balls to draw up. He knew he was going to come, there was no way to stop it. The last coherent thought he processed before filling Sam with his cum was that he would now be branded a premature ejaculator.

For his part, Sam was just completely shocked that Dean had come so quickly. “That good?” he asked. “Good enough to make you get off in two minutes?”

“Think it was closer to three”, Dean replied as he pulled out and lay down next to Sam with exhaustion.

“Gross, fuck, dude, seriously, I’ve got jizz dripping out of me. Christ. Would you get me a damn washcloth or something?” From the tone of his voice, Dean could almost see Sam’s bitchface, even though it was hidden in the pillows. Dean got up right away. Instead of just giving Sam a towel, he covered the cloth in warm water and returned to the bed to clean Sam up himself. 

That was when he realized his brother was still hard. Maybe that’s why he was grumpy. “Shit, man, I didn’t mean to leave you hanging like that. Sorry. I didn’t expect it either, that it would feel good enough to make me come so damn fast. Come on, let me take care of that for you.”  
Without waiting for an answer, he just turned Sam over onto his back, slid down the bed and took Sam’s hard cock into his mouth, hollowing his cheeks and humming and sucking for all he was worth. Bonus for the evening, Sam came as fast as Dean had, and that made Dean feel a little better. 

So now, of course, it was time for the You Just Fucked Me Up The Ass conversation he knew would follow. As always, Dean waited for Sam to initiate it, since he was the expert on the talky-talky. “That hurt. At first. But it did feel good, really, it did, I swear. I liked it. I’d like to do it again. Probably not for a few days, though”, he finished with a slight flush to his cheeks.

“Good. Yeah. We can just do it when you want, it doesn’t have to be all the time. It did really feel good, for me, anyway. And you know, we can, uh…(what the hell was the word he was trying to thinking of? Oh, right) _switch_? If you wanted to.”

“Well, since you thought it felt so good being inside me, then yeah, I want to know what it feels like to be inside you. We gotta make sure we always have plenty of that lube, though. I figure both of us will get more comfortable physically with it, but still…the uh, the **preparing** part seems pretty freaking important.”

Both of them breathed a sigh of relief. They’d gone through with it, and yeah, it was messy and inexpert and still just really damn strange, but they’d both liked it. 

Dean’s reply was almost lost in his yawning and exhaustion. “You…you were so good…you were so…”, no more words could form in Dean’s brain as he started to drift into sleep.

“Oh hell no”, Sam said, shaking Dean’s shoulder and hauling him up into a sitting position. “You can stay over here if you want but no fucking way am I sleeping in the wet spot.” He was already standing up and moving toward the other bed (they never got tired of the ‘two queens’ joke, especially since they’d started fooling around). 

Despite his exhaustion, Dean managed to get up and move onto the unused bed with Sam. They pulled the covers up over them, and right before sleep claimed him as well, Sam managed to get out “More research would probably be a good idea.”

All right, so it hadn’t been some kind of perfect, world-shaking, romantic experience. But they were both hoping that eventually it would.


End file.
